AU2014237862B2 - 1 -hydroxy-benzooxaboroles as antiparasitic agents - Google Patents

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Publication number

AU2014237862B2

AU2014237862B2 AU2014237862A AU2014237862A AU2014237862B2 AU 2014237862 B2 AU2014237862 B2 AU 2014237862B2 AU 2014237862 A AU2014237862 A AU 2014237862A AU 2014237862 A AU2014237862 A AU 2014237862A AU 2014237862 B2 AU2014237862 B2 AU 2014237862B2

Authority

AU

Australia

Prior art keywords

hydroxy

dihydrobenzo

oxaborol

trifluoromethoxy

benzamide

Prior art date

2013-03-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

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• 239000003096 antiparasitic agent Substances 0.000 title description 2
• 229940125687 antiparasitic agent Drugs 0.000 title description 2
• 239000000203 mixture Substances 0.000 claims abstract description 454
• 150000001875 compounds Chemical class 0.000 claims abstract description 149
• 150000003839 salts Chemical class 0.000 claims abstract description 112
• 238000000034 method Methods 0.000 claims abstract description 64
• 241001465754 Metazoa Species 0.000 claims abstract description 61
• 244000079386 endoparasite Species 0.000 claims abstract description 21
• 238000009472 formulation Methods 0.000 claims abstract description 21
• 206010061217 Infestation Diseases 0.000 claims abstract description 15
• -1 methoxy, amino Chemical group 0.000 claims description 96
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 22
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 17
• 150000002431 hydrogen Chemical group 0.000 claims description 14
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 7
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 5
• RWFSEDQTFFOUCC-UHFFFAOYSA-N n-[1-[(7-chloro-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C2COB(O)C2=C(Cl)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 RWFSEDQTFFOUCC-UHFFFAOYSA-N 0.000 claims description 5
• MJIVPJINKJIBDN-UHFFFAOYSA-N n-[2-cyano-1-[(7-ethyl-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CCC1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 MJIVPJINKJIBDN-UHFFFAOYSA-N 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• OHENQANLQNOMAO-UHFFFAOYSA-N oxaborole Chemical compound O1B=CC=C1 OHENQANLQNOMAO-UHFFFAOYSA-N 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• OONJIRYLEZIKJF-DEOSSOPVSA-N n-[(2s)-2-cyano-1-[(1-hydroxy-7-phenyl-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C([C@@](C)(NC(=O)C=1C=CC(OC(F)(F)F)=CC=1)C#N)OC1=CC=C2COB(O)C2=C1C1=CC=CC=C1 OONJIRYLEZIKJF-DEOSSOPVSA-N 0.000 claims description 3
• NPJJUCKDZYINDG-UHFFFAOYSA-N n-[1-[(4-chloro-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=2B(O)OCC=2C(Cl)=CC=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 NPJJUCKDZYINDG-UHFFFAOYSA-N 0.000 claims description 3
• UADNCSLBDXANMD-UHFFFAOYSA-N n-[1-[(7-bromo-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C2COB(O)C2=C(Br)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 UADNCSLBDXANMD-UHFFFAOYSA-N 0.000 claims description 3
• WDSAMJZWSDIUQV-UHFFFAOYSA-N n-[1-[(7-chloro-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-cyanobenzamide Chemical compound C=1C=C2COB(O)C2=C(Cl)C=1OCC(C)(C#N)NC(=O)C1=CC=C(C#N)C=C1 WDSAMJZWSDIUQV-UHFFFAOYSA-N 0.000 claims description 3
• OCFLGBVCCJHSMM-UHFFFAOYSA-N n-[1-[(7-chloro-5-fluoro-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound FC=1C=C2COB(O)C2=C(Cl)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 OCFLGBVCCJHSMM-UHFFFAOYSA-N 0.000 claims description 3
• CXUCDIOJYSSQSZ-UHFFFAOYSA-N n-[1-[[4-(aminomethyl)-7-chloro-1-hydroxy-3h-2,1-benzoxaborol-6-yl]oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C(CN)=C2COB(O)C2=C(Cl)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 CXUCDIOJYSSQSZ-UHFFFAOYSA-N 0.000 claims description 3
• DOLOZBKYANHYEN-UHFFFAOYSA-N n-[1-amino-3-[[4-(aminomethyl)-7-chloro-1-hydroxy-3h-2,1-benzoxaborol-6-yl]oxy]-2-methyl-1-oxopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C(CN)=C2COB(O)C2=C(Cl)C=1OCC(C)(C(N)=O)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 DOLOZBKYANHYEN-UHFFFAOYSA-N 0.000 claims description 3
• CCNKMQQKLJRJHY-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-4,7-dimethyl-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CC=1C=2B(O)OCC=2C(C)=CC=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 CCNKMQQKLJRJHY-UHFFFAOYSA-N 0.000 claims description 3
• YCHOCYWQBCSPAW-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-7-methoxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound COC1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 YCHOCYWQBCSPAW-UHFFFAOYSA-N 0.000 claims description 3
• KVQYOBJRWDCBDI-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-7-propyl-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CCCC1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 KVQYOBJRWDCBDI-UHFFFAOYSA-N 0.000 claims description 3
• QFZHKAZIIMACEO-UHFFFAOYSA-N n-[2-cyano-1-[(7-cyclopropyloxy-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(=O)NC(C#N)(C)COC1=CC=C2COB(O)C2=C1OC1CC1 QFZHKAZIIMACEO-UHFFFAOYSA-N 0.000 claims description 3
• XYAZJEDQJFSWEK-UHFFFAOYSA-N n-[2-cyano-1-[[1-hydroxy-7-(2,2,2-trifluoroethyl)-3h-2,1-benzoxaborol-6-yl]oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C2COB(O)C2=C(CC(F)(F)F)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 XYAZJEDQJFSWEK-UHFFFAOYSA-N 0.000 claims description 3
• JJPFLQJZQOMEDD-UHFFFAOYSA-N n-[2-cyano-1-[[1-hydroxy-7-(trifluoromethoxy)-3h-2,1-benzoxaborol-6-yl]oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C2COB(O)C2=C(OC(F)(F)F)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 JJPFLQJZQOMEDD-UHFFFAOYSA-N 0.000 claims description 3
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
• UADNCSLBDXANMD-SFHVURJKSA-N n-[(2s)-1-[(7-bromo-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound N([C@@](COC=1C(=C2B(O)OCC2=CC=1)Br)(C)C#N)C(=O)C1=CC=C(OC(F)(F)F)C=C1 UADNCSLBDXANMD-SFHVURJKSA-N 0.000 claims description 2
• CCQARZRSMGXIJC-UHFFFAOYSA-N n-[1-[(7-chloro-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethylsulfonyl)benzamide Chemical compound C=1C=C2COB(O)C2=C(Cl)C=1OCC(C)(C#N)NC(=O)C1=CC=C(S(=O)(=O)C(F)(F)F)C=C1 CCQARZRSMGXIJC-UHFFFAOYSA-N 0.000 claims description 2
• LMNXJBJQZIVVEQ-UHFFFAOYSA-N n-[1-[(7-chloro-1-hydroxy-5-methyl-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CC1=CC=2COB(O)C=2C(Cl)=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 LMNXJBJQZIVVEQ-UHFFFAOYSA-N 0.000 claims description 2
• YKDVFXAIAPCKBR-UHFFFAOYSA-N n-[1-[(7-chloro-4-fluoro-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C(F)=C2COB(O)C2=C(Cl)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 YKDVFXAIAPCKBR-UHFFFAOYSA-N 0.000 claims description 2
• CPCDDIVHQNJLJA-UHFFFAOYSA-N n-[1-[[4-(aminomethyl)-1-hydroxy-3h-2,1-benzoxaborol-6-yl]oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=2B(O)OCC=2C(CN)=CC=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 CPCDDIVHQNJLJA-UHFFFAOYSA-N 0.000 claims description 2
• ABARSGKCJXMWQY-UHFFFAOYSA-N n-[1-[[7-(aminomethyl)-1-hydroxy-3h-2,1-benzoxaborol-6-yl]oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C2COB(O)C2=C(CN)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 ABARSGKCJXMWQY-UHFFFAOYSA-N 0.000 claims description 2
• AXKGJRYZSVLMIY-UHFFFAOYSA-N n-[1-amino-3-[[7-(2-aminoethoxy)-1-hydroxy-3h-2,1-benzoxaborol-6-yl]oxy]-2-methyl-1-oxopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C2COB(O)C2=C(OCCN)C=1OCC(C)(C(N)=O)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 AXKGJRYZSVLMIY-UHFFFAOYSA-N 0.000 claims description 2
• CZXLYCOAHGCDRZ-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-7-methyl-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CC1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 CZXLYCOAHGCDRZ-UHFFFAOYSA-N 0.000 claims description 2
• ZBSWWHZLGUDSBC-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-7-phenoxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(=O)NC(C#N)(C)COC1=CC=C2COB(O)C2=C1OC1=CC=CC=C1 ZBSWWHZLGUDSBC-UHFFFAOYSA-N 0.000 claims description 2
• ZPKANNKVBAALHF-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-7-propan-2-yl-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CC(C)C1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 ZPKANNKVBAALHF-UHFFFAOYSA-N 0.000 claims description 2
• GMSIDRGKMVUZIN-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-7-thiophen-2-yl-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(=O)NC(C#N)(C)COC1=CC=C2COB(O)C2=C1C1=CC=CS1 GMSIDRGKMVUZIN-UHFFFAOYSA-N 0.000 claims description 2
• NLRMWWHECAMFGH-UHFFFAOYSA-N n-[2-cyano-1-[(4,7-dichloro-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C(Cl)=C2COB(O)C2=C(Cl)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 NLRMWWHECAMFGH-UHFFFAOYSA-N 0.000 claims description 2
• CEUFSBKCAOEBIH-UHFFFAOYSA-N n-[2-cyano-1-[(5,7-dichloro-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound ClC=1C=C2COB(O)C2=C(Cl)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 CEUFSBKCAOEBIH-UHFFFAOYSA-N 0.000 claims description 2
• NRKVYVVWIVZMOU-UHFFFAOYSA-N n-[2-cyano-1-[(7-cyclopropyl-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(=O)NC(C#N)(C)COC1=CC=C2COB(O)C2=C1C1CC1 NRKVYVVWIVZMOU-UHFFFAOYSA-N 0.000 claims description 2
• NNXRUTBIWKNHMU-UHFFFAOYSA-N n-[2-cyano-1-[[1-hydroxy-7-(trifluoromethyl)-3h-2,1-benzoxaborol-6-yl]oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C2COB(O)C2=C(C(F)(F)F)C=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 NNXRUTBIWKNHMU-UHFFFAOYSA-N 0.000 claims description 2
• MBWYIBRMNPJLCK-UHFFFAOYSA-N n-[2-cyano-1-[[7-(dimethylamino)-1-hydroxy-3h-2,1-benzoxaborol-6-yl]oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CN(C)C1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 MBWYIBRMNPJLCK-UHFFFAOYSA-N 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• MLJNLEHOUCYDAD-UHFFFAOYSA-N tert-butyl n-[2-[[6-[2-cyano-2-[[4-(trifluoromethoxy)benzoyl]amino]propoxy]-1-hydroxy-3h-2,1-benzoxaborol-7-yl]oxy]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCOC1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 MLJNLEHOUCYDAD-UHFFFAOYSA-N 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 5
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
• 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
• JJPFLQJZQOMEDD-SFHVURJKSA-N n-[(2s)-2-cyano-1-[[1-hydroxy-7-(trifluoromethoxy)-3h-2,1-benzoxaborol-6-yl]oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound N([C@@](COC=1C(=C2B(O)OCC2=CC=1)OC(F)(F)F)(C)C#N)C(=O)C1=CC=C(OC(F)(F)F)C=C1 JJPFLQJZQOMEDD-SFHVURJKSA-N 0.000 claims 1
• OFSHNDGNUCBDRZ-UHFFFAOYSA-N n-[1-[(7-chloro-1-hydroxy-4-methyl-3h-2,1-benzoxaborol-6-yl)oxy]-2-cyanopropan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound ClC=1C=2B(O)OCC=2C(C)=CC=1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 OFSHNDGNUCBDRZ-UHFFFAOYSA-N 0.000 claims 1
• OONJIRYLEZIKJF-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-7-phenyl-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(=O)NC(C#N)(C)COC1=CC=C2COB(O)C2=C1C1=CC=CC=C1 OONJIRYLEZIKJF-UHFFFAOYSA-N 0.000 claims 1
• KOHMPLFUKMPLJI-UHFFFAOYSA-N n-[2-cyano-1-[(1-hydroxy-7-propan-2-yloxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CC(C)OC1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 KOHMPLFUKMPLJI-UHFFFAOYSA-N 0.000 claims 1
• NXTZTQQZGKFGLR-UHFFFAOYSA-N n-[2-cyano-1-[(7-ethoxy-1-hydroxy-3h-2,1-benzoxaborol-6-yl)oxy]propan-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound CCOC1=C2B(O)OCC2=CC=C1OCC(C)(C#N)NC(=O)C1=CC=C(OC(F)(F)F)C=C1 NXTZTQQZGKFGLR-UHFFFAOYSA-N 0.000 claims 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
• 239000000243 solution Substances 0.000 description 404
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 346
• 239000000047 product Substances 0.000 description 327
• 239000007787 solid Substances 0.000 description 293
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 270
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 242
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 228
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 217
• 229910001868 water Inorganic materials 0.000 description 199
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 185
• 239000011541 reaction mixture Substances 0.000 description 183
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 176
• 230000002829 reductive effect Effects 0.000 description 166
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 121
• 235000019439 ethyl acetate Nutrition 0.000 description 114
• 239000004698 Polyethylene Substances 0.000 description 111
• 238000004440 column chromatography Methods 0.000 description 107
• 239000002904 solvent Substances 0.000 description 105
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 103
• 239000000741 silica gel Substances 0.000 description 96
• 229910002027 silica gel Inorganic materials 0.000 description 96
• 239000012267 brine Substances 0.000 description 94
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 94
• 239000012044 organic layer Substances 0.000 description 92
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 80
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